Total synthesis of racemic and (R) and (S)-4-methoxyalkanoic acids and their antifungal activity

The total synthesis of 4-methoxydecanoic acid and 4-methoxyundecanoic acid in racemic and stereoselective [(R) and (S)] forms has been accomplished. For stereoselective synthesis of the compounds (S) and (R)-BINOL complexes have been used to generate the required chiral centres. The antifungal activity of these compounds has been studied against different organisms and the results were found to be impressive. The activity of the compounds in racemic and in stereoselective forms was compared. (R)-4-Methoxydecanoic acid was found to be most potent (MIC: 0.019 mg/mL against Candida albicans MTCC 227, C. albicans MTCC 4748, Aspergillus brasiliensis (niger) MTCC 281 and Issatchenkia orientalis MTCC 3020).

Graphical abstractThe total synthesis of 4-methoxyalkanoic acids has been achieved in racemic and stereoselective [(R) and (S)] forms. The antifungal activity of the compounds was examined. (R)-4-Methoxydecanoic acid was found to be most potent. Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► The total synthesis of 4-methoxyalkanoic acids in racemic and stereoselective forms. ► Application of (S) and (R)-BINOL complexes to generate the required stereocenters. ► Impressive antifungal activity of these compounds against different organisms. ► Comparison of the activity of the compounds in racemic and stereoselective forms. ► (R)-4-Methoxydecanoic acid as the most potent compound.